ISSN:
0749-1581
Keywords:
Cyclohexanone-cinnamaldehyde
;
condensation
;
2,4-Disubstituted
;
bicyclo[3.3.1]nonan-9-ones
;
Conforniational analysis
;
Application of 1H Homo-COSY
;
Chemistry
;
Analytical Chemistry and Spectroscopy
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Condensation of substituted cyclohexanones with cinnamaldehydes and morpholine in the presence of anhydrous cerium(III) chloride was carried out. The stereochemistry of the condensed products, variously substituted 2-morpholino-4-phenylbicyclo[3.3.1]nonan-9-ones, was deduced by using the 1H NMR COSY technique and 13C NMR data. In order to draw a general conclusion, the stereochemistry of the sterically comparable 2,4-diphenylbicyclo[3.3.1]nonan-9-one was also studied in detail, using 1H NMR COSY and 13C NMR data. A general conclusion regarding the boat-chair conformational preference for such sterically comparable cis-2,4-disubstituted bicyclo[3.3.1]nonan-9-ones has been deduced, with the substituted ring in the boat form and a diequatorial disposition of the two substituents.
Additional Material:
5 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/mrc.1260251107
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